DRM stands for Digitial Rights Management. What this means is that one of your files (MP3 or more likely a WMA) is protected and can't be copied. You can check which ones are by right clicking on each file, and selecting properties. You will see the word 'protected'. At the side of that it will say either YES or NO. If it says YES you can't copy the file. Most music files that are protected are WMA files. These were sold at download stores, apart from I-Tunes who used a different file system. Most sites have now replaced them with none protected MP3.
The only way round copying a protected audio is to re-record it with audio recording software such as DanDans Audio Editor etc. You play it back and record, then save it as an MP3.
There is software that will convert them, but unless you have loads of protected files, I wouldn't bother looking for it as you have to pay for the convertor.

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When the message 'Error' or 'License Issue' shows,
it is referring to the DRM (Digital Rights Management) licences which are
commonly found when downloading files. This is a method the music companies use
to protect their music

sounds like the music you put on it is full of DRM. You can either rip the music off the original cd to mp3 and not include DRM. Or you can request a non DRM version download from where you downloaded it to begin with.

Your song (.WMA) are copy protected by 'Microsoft Windows Media digital
rights management (DRM)' and appears to be requesting a license key which needs to be loaded to your player.Solution:
- Media Player will automatically load those licences keys to your player for your authorised music/media files.- Alternatively, remove DRM (for song that you own ...) by some third party
means software (including burning them on CD with appropriate options)- Use alternative songs encoding (such as .mp3) that do not this
protection.

These songs must have been purchased online. Itunes, or many online MP3 stores do this to prevent piracy. The songs can only be played on the PC that purchased them. Either buy the music from a DRM free site or find a DRM ripper, which maybe illegal in some locations.

If it does it on all CD's then it could be somekind of error on the MP3 device itself. However if only on selected discs, than it's the disc which incorporates anti copying tecnology, in which case you'll have to find another way of carrying out (which is illegal by the way) the transfer, unless you pay for a licence!
D.R.M. stands for Digital Rights Management, by the way.

In your Windows media Player go into tools and select options. Select rip music and untick copy protect music. The music you have in WMP wont work. you will have to put them in again after you made the changes. Hope this helps